Building AI Boston

Boston has no shortage of people building ambitious AI products. The harder part is turning those ideas into companies and technologies that can actually work, scale, and succeed inside an enterprise. That’s where the Open Accelerator comes in. The new Massachusetts initiative is designed to help early-stage AI companies bridge the gap between promising prototypes and real-world adoption. Our guest, Stefanie Chiras, brings an unusually deep perspective to that challenge. She began her career working on the materials and technology inside silicon chips, moved progressively up the technology stack, and eventually led major businesses and ecosystem work at Red Hat. Today, she is helping build the Open Accelerator around many of the same principles that made open source transformative: shared knowledge, strong communities, clear standards, and the idea that innovation gets better when more people can contribute. The Open Accelerator brings together Red Hat, the Massachusetts AI Hub, IBM Ventures, founders, investors, technical experts, and others across the Massachusetts innovation ecosystem. Its 16-week residency gives selected AI startups access to business and technical mentors, enterprise expertise, connections, and a community designed to help them move faster without requiring them to give up equity simply to participate. We dig into: • Why AI has dramatically accelerated the journey from idea to prototype, but not necessarily from prototype to successful product • What open source can teach us about building AI communities and ecosystems • Stefanie’s journey from materials science and silicon chips to software, product leadership, and the Red Hat ecosystem • How Red Hat helped make open-source technology enterprise-ready, and why that history matters for AI startups today • Why Boston and Massachusetts have an opportunity to become a place where people not only come to learn, but stay to build and grow • How the Open Accelerator helps founders with enterprise technology, sales, mentorship, connections, and funding opportunities • Why participation in the accelerator does not require founders to give up equity • What the Open Accelerator’s first cohort is teaching the team, and what comes next • Why strong guardrails can actually encourage AI experimentation rather than restrict it • The role government, universities, companies, investors, and community organizations can play in creating a stronger AI ecosystem This conversation is about what happens after the prototype. It’s about the infrastructure, expertise, relationships, and community that help good ideas become viable companies, and why Massachusetts may be particularly well positioned to build that kind of ecosystem. LINKS: https://the-open-accelerator.com Learn more about your ad choices. Visit megaphone.fm/adchoices

What does it take to build an AI ecosystem that starts in one place but reaches far beyond it? That’s the idea behind Boston AI Week, the community-driven festival Judah Phillips created to connect companies, academics, investors, government, cultural institutions, job seekers, students, and people who are simply curious about AI. Judah is Chief AI and Product Officer at Market Holdings and has been building AI communities in Boston for years. This year, Boston AI Week includes more than 500 participating organizations and more than 150 events, with visitors and delegations coming from 23 countries. Boston is the home base, but increasingly it isn’t the boundary. What makes the event unusual is the model. Judah deliberately rejected the traditional conference format in favor of something decentralized, largely free, and built by the community itself. He describes it as a “civic action.” Building AI Boston is part of that ecosystem too: Kara serves on the Boston AI Week board, and Kara and Anna will be on site as official media partners. We dig into: • Why an AI ecosystem can’t just be software companies talking to other software companies • The four goals behind Boston AI Week: broaden understanding, create jobs, connect the ecosystem, and strengthen the Massachusetts economy • Why Judah built a decentralized festival instead of a traditional conference • Why keeping most events free matters to the mission • How Boston AI Week became an international draw • The career fair, and why job creation matters in a conversation often dominated by job loss • Judah’s bigger ambition to make AI part of business, culture, community, and everyday life • Why he prefers “humans in control” to simply “human in the loop” This conversation is really about who gets to participate in the AI economy, how you build the connections that make an ecosystem work, and what happens when you invite a much bigger group of people into the conversation. Boston AI Week https://aiweek.bostonBoston AI Week Schedule: https://aiweek.boston/scheduleJudah's Linkedin: https://www.linkedin.com/in/judahphillips Learn more about your ad choices. Visit megaphone.fm/adchoices

In this exciting episode of Building AI Boston, hosts Anna and Chris sit down with AI marketing strategist, speaker, and entrepreneur Molly Mahoney to explore how artificial intelligence is transforming the way businesses connect, communicate, and grow. Known as “The Prepared Performer,” Molly has helped thousands of entrepreneurs leverage AI, content creation, and authentic storytelling to build profitable businesses while staying true to their unique voice. Her viral content has generated millions of views, and she has been featured in Forbes, Entrepreneur, Inc., and major marketing conferences around the world. During this conversation, Molly shares: • How to use AI without sounding robotic • The future of content creation and marketing • Why authenticity matters more than ever in the AI era • Building meaningful relationships with AI-powered tools • AI workflows that save time and increase impact • How entrepreneurs can stand out in a world flooded with AI-generated content • Why your “weird” may be your greatest competitive advantage Whether you’re an entrepreneur, marketer, creator, business leader, or simply curious about the future of AI, this episode is packed with actionable insights and inspiration. SPECIAL GIVEAWAY: Molly.live/aiboston Learn more about Molly Mahoney: https://www.mollymahoney.com The Prepared Performer: https://www.thepreparedperformer.com Listen to more episodes of Building AI Boston: https://www.buildingaiboston.com Subscribe for more conversations with the leaders shaping the future of artificial intelligence. Learn more about your ad choices. Visit megaphone.fm/adchoices

AI is really good at coming up with plans. It's not always great at executing them. David Wong thinks that gap is the whole story for legal AI right now, and it's why Thomson Reuters has been building the way they have. David is Chief Product Officer at Thomson Reuters, which has been around for over a hundred years and is one of the most established names in legal information. He leads CoCounsel, their AI platform, which recently hit 1 million users across 107 countries. He also just published a widely read Fortune piece laying out his framework for where legal AI is heading. We recorded the day after Anthropic launched Claude for the Legal Industry, with both Thomson Reuters and Descrybe included as MCP connectors. So this is a conversation about what it looks like when a 100-year-old company and a three-year-old startup end up in the same lineup, and what separates purpose-built legal AI from generic tools. We dig into: • The plan vs. execution gap at the center of David's Fortune piece, and why generic AI tools often stumble at the second part • The "wrong tool for the problem" framing, and why hallucination isn't the real risk; choosing the wrong tool is • Why both Descrybe and Thomson Reuters count as purpose-built tools, even though they sit at very different ends of the legal tech market • Thomson Reuters's "we replaced ourselves" moment: rebuilding Westlaw on a generative AI foundation, and why staying still wasn't an option • The PC software ecosystem analogy David uses to explain where this is all heading, and why no single AI company is going to write every legal application • Claude as orchestrator, not soloist: what it looks like when frontier AI delegates to a "team of specialists" through MCP connectors • The access to justice payoff both ends of the legal tech market are betting on David has been at the front of Thomson Reuters's AI strategy from the beginning, and his Fortune piece moved a chunk of the current debate about how AI actually executes on legal work. But this conversation stays grounded in customers, coexistence, and what it actually takes to ship this stuff responsibly at scale. Learn more about your ad choices. Visit megaphone.fm/adchoices

Traditional conferences put everyone in one venue and hand them a ticket. Tech Week flips it: hundreds of events across a city, hosted by whoever wants to host, all on a single calendar. Rose Johnson thinks this format gives the power back to creators, and Boston is about to find out what that looks like. Rose is a marketing partner at Andreessen Horowitz, where she leads Tech Week, a16z's decentralized conference series that started in LA in 2022 and has expanded to four cities. Boston is the newest. They set an internal goal of 500 events for the debut. They blew past 600. We recorded ahead of Boston Tech Week (May 26 to 31), which runs back-to-back with New York Tech Week so attendees can do both. This is a conversation about why Boston was the next city, what a "platform not organizer" model actually looks like, and what to expect when 600 plus events take over a town that's never done this before. We dig into: The origin story of Tech Week, from a post-COVID LA experiment in 2022 to a four-city circuit Why the decentralized format works, and why "power back to the creators" is the whole point Boston's response, well past the internal 500-event target, with deep tech and biotech sharing the calendar with hackathons for marketers What it means to treat Tech Week as a platform rather than a conference, with hosts setting the format and a16z staying out of the way The "renaissance, not revolution" framing, and why collaboration between cities matters more than rivalry How each city develops its specialization, from LA's entertainment AI and defense clusters to whatever Boston ends up becoming known for Practical advice for founders, students, and curious newcomers on how to navigate 600 plus events with a mindset of abundance Rose has been on the Tech Week team since the beginning and has watched it go from one LA experiment to a four-city circuit that companies like Anthropic, OpenAI, and Axios now return to year after year. But this conversation stays grounded in Boston specifically: the calendar, the hosts, the people showing up, and what the city gets to put on the map. Learn more about Boston Tech Week: https://www.tech-week.com/boston View the official Boston Tech Week schedule: https://www.tech-week.com/calendar/bo... Learn more about Rose Johnson at a16z: https://a16z.com/author/rose-johnson/ Boston Tech Week is presented by a16z and is scheduled for May 26 to May 31, 2026, with events hosted by companies and organizations throughout the city. Rose Johnson is listed by a16z as a marketing partner supporting Tech Week for a16z speedrun. Tech Week calendar + dedicated tracks: tech-week.com/calendar/boston Tech Week website: www.tech-week.com speedrun: a16z.speedrun.com Tech Week socials X: https://x.com/Techweek_ LinkedIn: / tech-week-a16z Instagram: / techweeka16z My linkedin if you need it: / rosejohnson32 Learn more about your ad choices. Visit megaphone.fm/adchoices